Improved procedure for the oxidative cleavage of olefins by OsO 4-NaIO4

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3217-3219

  Yu, Wensheng ^a   Mei, Yan ^a   Kang, Ying ^a   Hua, Zhengmao ^a   Jin, Zhendong ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DIOXANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DEGRADATION; OXIDATION; REACTION ANALYSIS;

ALDEHYDES; ALKENES; CATALYSIS; CHEMISTRY, ORGANIC; IODATES; MOLECULAR STRUCTURE; OSMIUM COMPOUNDS; OXIDATION-REDUCTION; PYRIDINES;

EID: 4644228335     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0400342     Document Type: Article

References (11)

1. Yu, W.; Zhang, Y.; Jin. Z. Org. Lett. 2001, 3, 1447.
2. Pappo, R.: Alen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478.
3. (a) Grant, P. K.; Hanton, L. R.; Lynch, G. P.; Robinson, W. T.; Wong, G. Aust. J. Chem. 1994, 47, 71.
4. (b) Lohray, B. B.; Bhushan, V.; Kumar, R. K. J. Org. Chem. 1994, 59, 1375.
5. There are numerous examples of using the two-step procedure to cleave olefins. The following are some of the recent applications: (a) Francavilla, C.; Chen, W.; Kinder, F. R. Jr. Org. Lett. 2003, 5, 1233. (b) Wang, Z.; Moloney, M. G. Tetrahedron Lett. 2002, 43, 9629. (c) Taylor, R. E.; Chen, Y.; Beatty, A. J. Am. Chem. Soc. 2003, 125, 26. (d) Roush, W. R.; Bannister, T. D.; Wendt, M. D.; Jablonowski, J. A.; Scheidt, K. A. J. Org. Chem. 2002, 67, 4275.
6. There are numerous examples of using the two-step procedure to cleave olefins. The following are some of the recent applications: (a) Francavilla, C.; Chen, W.; Kinder, F. R. Jr. Org. Lett. 2003, 5, 1233. (b) Wang, Z.; Moloney, M. G. Tetrahedron Lett. 2002, 43, 9629. (c) Taylor, R. E.; Chen, Y.; Beatty, A. J. Am. Chem. Soc. 2003, 125, 26. (d) Roush, W. R.; Bannister, T. D.; Wendt, M. D.; Jablonowski, J. A.; Scheidt, K. A. J. Org. Chem. 2002, 67, 4275.
7. There are numerous examples of using the two-step procedure to cleave olefins. The following are some of the recent applications: (a) Francavilla, C.; Chen, W.; Kinder, F. R. Jr. Org. Lett. 2003, 5, 1233. (b) Wang, Z.; Moloney, M. G. Tetrahedron Lett. 2002, 43, 9629. (c) Taylor, R. E.; Chen, Y.; Beatty, A. J. Am. Chem. Soc. 2003, 125, 26. (d) Roush, W. R.; Bannister, T. D.; Wendt, M. D.; Jablonowski, J. A.; Scheidt, K. A. J. Org. Chem. 2002, 67, 4275.
8. There are numerous examples of using the two-step procedure to cleave olefins. The following are some of the recent applications: (a) Francavilla, C.; Chen, W.; Kinder, F. R. Jr. Org. Lett. 2003, 5, 1233. (b) Wang, Z.; Moloney, M. G. Tetrahedron Lett. 2002, 43, 9629. (c) Taylor, R. E.; Chen, Y.; Beatty, A. J. Am. Chem. Soc. 2003, 125, 26. (d) Roush, W. R.; Bannister, T. D.; Wendt, M. D.; Jablonowski, J. A.; Scheidt, K. A. J. Org. Chem. 2002, 67, 4275.
9. Criegee, R.; Marchand, B.; Wannowlus, H. Justus Liebigs Ann. Chem. 1942, 550, 99.
10. (b) Schroder, M. Chem. Rev. 1980, 80, 187 and references therein.
11. All compounds were fully characterized.